CN110927207A - Method for testing photoresist resin component - Google Patents
Method for testing photoresist resin component Download PDFInfo
- Publication number
- CN110927207A CN110927207A CN201911191617.5A CN201911191617A CN110927207A CN 110927207 A CN110927207 A CN 110927207A CN 201911191617 A CN201911191617 A CN 201911191617A CN 110927207 A CN110927207 A CN 110927207A
- Authority
- CN
- China
- Prior art keywords
- monomer
- photoresist resin
- spectrum
- ester
- photoresist
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 61
- 229920005989 resin Polymers 0.000 title claims abstract description 61
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000012360 testing method Methods 0.000 title abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 83
- 238000001228 spectrum Methods 0.000 claims abstract description 25
- 230000004580 weight loss Effects 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 238000005481 NMR spectroscopy Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- -1 adamantyl derivative ester Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 238000002411 thermogravimetry Methods 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 4
- 238000010998 test method Methods 0.000 claims description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 abstract description 13
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 abstract description 4
- 238000002076 thermal analysis method Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
- G01N25/20—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
- G01N24/087—Structure determination of a chemical compound, e.g. of a biomolecule such as a protein
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/44—Resins; Plastics; Rubber; Leather
- G01N33/442—Resins; Plastics
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N5/00—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid
- G01N5/04—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid by removing a component, e.g. by evaporation, and weighing the remainder
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- High Energy & Nuclear Physics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the field of photoresist resin, and particularly relates to a method for testing components of photoresist resin, which comprises the following steps: s1, dissolving the photoresist resin to be tested in a solvent, and obtaining a hydrogen spectrum and a carbon spectrum through nuclear magnetic resonance; s2, analyzing a hydrogen spectrum and a carbon spectrum, if monomer peaks in the spectrum do not overlap with each other, obtaining the molar ratio of each monomer in the photoresist resin according to peak areas, and if the monomer peaks in the spectrum overlap with each other, switching to S3; and S3, performing thermal weight loss analysis on the photoresist resin to be tested, and calculating the molar ratio of each monomer in the photoresist resin. The invention has the beneficial effects that: when the characteristic peaks overlap and cannot be distinguished in FTIR tests by other testing means such as HNMR tests, thermal analysis can be used as an accurate analysis method for analyzing the components of the photoresist resin.
Description
Technical Field
The invention belongs to the field of photoresist resin, and particularly relates to a method for testing components of photoresist resin.
Background
Photoresist resins are currently a key material for the fabrication of advanced integrated circuits. The film forming material of the photoresist is various photoresist resins, such as phenolic resin, methacrylic resin and the like. The photoresist resin has excellent properties such as high temperature resistance, corrosion resistance and the like. The photoresist resin is prepared by copolymerizing 1-4 functional monomers, each functional monomer endows the photoresist with excellent application performance, and photoetching patterns required to be manufactured are smaller and smaller along with miniaturization of components. The proportion of each functional monomer is required to be controlled by photoresist resin when the small-size pattern is manufactured, a certain feeding ratio is generally set during the design and research and development of the photoresist resin, and after the resin is polymerized, each monomer group is required to be controlled within a certain range (the difference between the feeding ratio and the set feeding ratio is not large) so that excellent performance can be maintained.
At present, nuclear magnetic analysis, FTIR analysis and the like are mainly used for analyzing and testing resin polymers, wherein the nuclear magnetic analysis can analyze the content of H and C in the polymer structure, but the resin polymers need to be dissolved in a special reagent, some resins are extremely difficult to dissolve, monomer peaks of a nuclear magnetic spectrum of a photoresist polymer can influence each other and shift, a plurality of peaks can overlap, and the analysis cannot be carried out if the characteristic peaks of polymer components overlap; the preparation work in the early stage of FTIR infrared test analysis is more, and the operation is more complicated.
Disclosure of Invention
In order to solve the problems, the invention provides a method for testing components of a photoresist resin, which analyzes the proportion of each component according to the weight loss condition of a polymer on a thermal analysis chart and provides a new photoresist resin component analysis approach when the coincidence of characteristic peaks of a nuclear magnetic analysis chart cannot be analyzed.
The invention provides the following technical scheme:
a method of testing a photoresist resin composition comprising the steps of:
s1, dissolving the photoresist resin to be tested in a solvent, and obtaining a hydrogen spectrum and a carbon spectrum through nuclear magnetic resonance;
s2, analyzing a hydrogen spectrum and a carbon spectrum, if monomer peaks in the spectrum do not overlap with each other, obtaining the molar ratio of each monomer in the photoresist resin according to peak areas, and if the monomer peaks in the spectrum overlap with each other, switching to S3;
s3, performing thermogravimetric analysis on the photoresist resin to be tested, calculating the molar ratio of each monomer in the photoresist resin by the following notations,
wherein, A% is the mole percentage of the photoresist resin monomer A, B% is the mole percentage of the photoresist resin monomer B, Tg1Is the weight loss percentage, Tg, of the photoresist resin in the first stage of the thermal weight loss process2Is the weight loss percentage of the second stage of the photoresist resin in the thermal weight loss process, TA1Is the weight loss percentage of the monomer A in the first stage of the thermal weight loss process, MAIs the molar mass of the monomer A, MBIs the molar mass of the monomer B.
Preferably, the photoresist resin is polymerized by methacrylate monomer containing functional group, the structural general formula of the methacrylate monomer is as follows,
in the formula, R1Is H or a carbon-containing group having 1 to 20 carbon atoms, R2Is a functional group containing a functional group.
Preferably, the functional group is any one of a polar monomer, a rigid monomer, an acid-protecting monomer and a flexible monomer.
Preferably, R2 has 6-30 carbon atoms;
wherein all hydrogen atoms of carbon atoms connected with oxygen atoms of ester bonds are substituted by other groups to form one or more of tert-butyl ester, substituted tert-butyl ester, alkyl-substituted adamantyl derivative ester, alkyl-substituted norbornyl derivative ester, alkyl-substituted cyclic alkyl ester and alkyl-substituted cyclic alkyl derivative ester;
or the derivative is connected with an ester bond oxygen atom to form one or more of adamantyl ester containing 1 or more independent hydroxyl groups, cyclohexyl containing 1 or more independent hydroxyl groups, cyclopentyl containing 1 or more independent hydroxyl groups, polycyclicester compound containing 1 or more independent hydroxyl groups, caged ester compound containing 1 or more independent hydroxyl groups, butyrolactone, valerolactone, substituted valerolactone, caprolactone, substituted caprolactone, lactone containing adamantane structure, lactone containing polycyclic structure and lactone containing caged structure.
Preferably, the photoresist resin is prepared by a method comprising,
two methacrylate monomers A, B are subjected to RAFT reaction by taking azobisisoheptonitrile as an initiator, and the method comprises the following steps:
s1, heating tetrahydrofuran to 50-80 ℃ to obtain preheated tetrahydrofuran;
s2, dissolving the monomer and the initiator in tetrahydrofuran to obtain a tetrahydrofuran solution of the raw material;
s3, dropwise adding the tetrahydrofuran solution of the raw material obtained in the step S2 into the preheated tetrahydrofuran obtained in the step S1, and carrying out constant-temperature reflux reaction at the temperature of 50-80 ℃ for 10-30 hours;
s4, cooling to 20-30 ℃ after the reaction is finished, precipitating with n-hexane, filtering and drying to obtain the photoresist resin.
The invention has the beneficial effects that:
1. when the characteristic peaks overlap and cannot be distinguished in FTIR tests by other testing means such as HNMR tests, thermal analysis can be used as an accurate analysis method for analyzing the components of the photoresist resin.
2. The thermogravimetric analysis test can be finished within 0.5-2h of one sample, the resin is a solid sample generally, thermal analysis can be directly carried out, a solvent is not required to be screened to dissolve the solid, the sample preparation step and the solvent consumption are omitted, the operation is simple and convenient, the map is clear, and the analysis is easy.
3. The invention provides a method for testing components of photoresist resin, and provides a new method for testing and characterizing the photoresist resin.
Drawings
FIG. 1 is a TG curve of monomer A in example 1;
FIG. 2 is a TG curve of monomer B in example 1;
FIG. 3 is a TG curve of a photoresist resin in example 1;
FIG. 4 is a TG curve of monomer A in example 2;
FIG. 5 is a TG curve of monomer B in example 2;
FIG. 6 is a TG curve of the photoresist resin in example 2.
Detailed Description
The present invention will be described in detail with reference to the following examples.
Example 1
The methacrylate monomer A, B was polymerized by the method of the invention according to the monomer design molar ratio of 50:50 to obtain the photoresist resin.
The photoresist numerical value is analyzed through the nuclear magnetic resonance technology to obtain a hydrogen spectrum and a carbon spectrum, and the fact that monomer peaks in the spectrum are easily overlapped or interfered by a foreign peak is found, and the actual molar ratio of the monomers is not easy to obtain through the peak area.
The monomer A, the monomer B and the photoresist are subjected to thermal weight loss analysis respectively, a NETZSCH STA 449F5 thermal analyzer (Shanghai Town-Schleich Co., Ltd.) is adopted as the analyzer, the test temperature is 500 ℃, the heating rate is 20k/min, and the nitrogen protection is 20ml/min, so that the figures 1, 2 and 3 are obtained.
As can be seen from FIGS. 1 and 2, the decomposition of the monomer A started from 200 ℃ and the decomposition of the monomer B started from 330 ℃, and as shown in FIG. 3, the mass loss in the first stage of the resin C-TG curve was 28.24% (before 330 ℃), and from the two thermogravimetric plots 1 and 2, the decomposition of the monomer A was 65.1% before 330 ℃ and the decomposition of the monomer B was not completed before 330 ℃. Substituting the data into a monomer molar ratio calculation formula according to the first-stage weight loss 28.24 and the second-stage weight loss 64.22 of the resin in the map 3,
the calculation can be carried out to calculate that the monomer A and the monomer B are 50.22:49.78, the monomer feeding molar ratio during the resin polymerization is 50:50, and the two data are quite consistent.
TABLE 1
| Monomer | Single material feeding ratio | Thermogravimetric analysis molar ratio |
| A：B | 50:50 | 50.22:49.78 |
Example 2
The methacrylate monomer A, B was polymerized by the method of the invention according to the monomer design molar ratio of 70:30 to obtain the photoresist resin.
And analyzing the photoresist numerical value by a nuclear magnetic resonance technology to obtain a hydrogen spectrum and a carbon spectrum, and finding that the monomer peaks in the spectrum are mutually overlapped, so that the actual molar ratio of the monomer cannot be obtained through the peak area.
The monomer A, the monomer B and the photoresist are subjected to thermal weight loss analysis respectively, a NETZSCH STA 449F5 thermal analyzer (Shanghai Town-Schleich Co., Ltd.) is adopted as the analyzer, the test temperature is 500 ℃, the heating rate is 20k/min, and the nitrogen protection is 20ml/min, so that the graphs in FIG. 4, FIG. 5 and FIG. 6 are obtained.
As can be seen from FIGS. 4 and 5, the decomposition of the monomer A started from 200 ℃, the decomposition of the monomer B started from 330 ℃ or higher, the decomposition of the monomer A started from 200 ℃ and the decomposition of the monomer B started from 330 ℃ or higher, and as shown in FIG. 6, the mass loss in the first stage of the resin C-TG curve was 42.86% (before 330 ℃), and from the two thermogravimetric plots 4 and 5, the decomposition of the monomer A before 330 ℃ was 65.1%, while the decomposition of the monomer B before 330 ℃ was not observed. Substituting the data into a monomer molar ratio calculation formula according to the first-stage weight loss 42.86 and the second-stage weight loss 56.35 of the resin in the map 6,
monomer a to monomer B was calculated to be 69.25: 30.75, the molar ratio of monomer A to monomer B in the resin polymerization is 70:30, and the data of the monomer A to the monomer B are very close to that of the monomer B.
TABLE 2
| Monomer | Single material feeding ratio | Thermogravimetric analysis molar ratio |
| A：B | 70:30 | 69.25:30.75 |
The specific structural formulas of the monomers A and B are as follows,
although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (5)
1. A method of testing a resin component of a photoresist comprising the steps of:
s1, dissolving the photoresist resin to be tested in a solvent, and obtaining a hydrogen spectrum and a carbon spectrum through nuclear magnetic resonance;
s2, analyzing a hydrogen spectrum and a carbon spectrum, if monomer peaks in the spectrum do not overlap with each other, obtaining the molar ratio of each monomer in the photoresist resin according to peak areas, and if the monomer peaks in the spectrum overlap with each other, switching to S3;
s3, performing thermogravimetric analysis on the photoresist resin to be tested, calculating the molar ratio of each monomer in the photoresist resin by the following notations,
a% is the mole percentage of the photoresist resin monomer A, B% is the mole percentage of the photoresist resin monomer B, Tg1Is the weight loss percentage, Tg, of the photoresist resin in the first stage of the thermal weight loss process2Is the weight loss percentage of the second stage of the photoresist resin in the thermal weight loss process, TA1Is the weight loss percentage of the monomer A in the first stage of the thermal weight loss process, MAIs the molar mass of the monomer A, MBIs the molar mass of the monomer B.
2. The method of claim 1, wherein the photoresist resin is polymerized from a functional group-containing methacrylate monomer having the following general structural formula,
in the formula, R1Is H or a carbon-containing group having 1 to 20 carbon atoms, R2Is a functional group containing a functional group.
3. The method of claim 2, wherein the functional group is any one of a polar monomer, a rigid monomer, an acid-protecting monomer, and a flexible monomer.
4. The method of claim 2, wherein R2 has between 6 and 30 carbon atoms;
wherein all hydrogen atoms of carbon atoms connected with oxygen atoms of ester bonds are substituted by other groups to form one or more of tert-butyl ester, substituted tert-butyl ester, alkyl-substituted adamantyl derivative ester, alkyl-substituted norbornyl derivative ester, alkyl-substituted cyclic alkyl ester and alkyl-substituted cyclic alkyl derivative ester;
or the derivative is connected with an ester bond oxygen atom to form one or more of adamantyl ester containing 1 or more independent hydroxyl groups, cyclohexyl containing 1 or more independent hydroxyl groups, cyclopentyl containing 1 or more independent hydroxyl groups, polycyclicester compound containing 1 or more independent hydroxyl groups, caged ester compound containing 1 or more independent hydroxyl groups, butyrolactone, valerolactone, substituted valerolactone, caprolactone, substituted caprolactone, lactone containing adamantane structure, lactone containing polycyclic structure and lactone containing caged structure.
5. The method of testing the composition of a photoresist resin according to claim 1, wherein the photoresist resin is prepared by the following method,
two methacrylate monomers A, B are subjected to RAFT reaction by taking azobisisoheptonitrile as an initiator, and the method comprises the following steps:
s1, heating tetrahydrofuran to 50-80 ℃ to obtain preheated tetrahydrofuran;
s2, dissolving the monomer and the initiator in tetrahydrofuran to obtain a tetrahydrofuran solution of the raw material;
s3, dropwise adding the tetrahydrofuran solution of the raw material obtained in the step S2 into the preheated tetrahydrofuran obtained in the step S1, and carrying out constant-temperature reflux reaction at the temperature of 50-80 ℃ for 10-30 hours;
s4, cooling to 20-30 ℃ after the reaction is finished, precipitating with n-hexane, filtering and drying to obtain the photoresist resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911191617.5A CN110927207B (en) | 2019-11-28 | 2019-11-28 | Method for testing photoresist resin component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911191617.5A CN110927207B (en) | 2019-11-28 | 2019-11-28 | Method for testing photoresist resin component |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110927207A true CN110927207A (en) | 2020-03-27 |
| CN110927207B CN110927207B (en) | 2022-05-06 |
Family
ID=69846771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911191617.5A Active CN110927207B (en) | 2019-11-28 | 2019-11-28 | Method for testing photoresist resin component |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110927207B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112557640A (en) * | 2020-12-28 | 2021-03-26 | 中蓝晨光化工有限公司 | Method for testing degree of substitution of condensed type silicone resin |
| CN113030148A (en) * | 2021-03-24 | 2021-06-25 | 浙江省林业科学研究院 | Microscopic on-line detection method for phase state change of water-soluble low-molecular-weight resin |
| CN113804867A (en) * | 2021-09-27 | 2021-12-17 | 上海彤程电子材料有限公司 | Method for testing photoresist resin component |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN102830589A (en) * | 2012-08-23 | 2012-12-19 | 京东方科技集团股份有限公司 | Resin composition of negative photoresist and preparation method thereof |
| CN103995436A (en) * | 2013-02-15 | 2014-08-20 | 三星显示有限公司 | Photosensitive resin composition |
-
2019
- 2019-11-28 CN CN201911191617.5A patent/CN110927207B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN102830589A (en) * | 2012-08-23 | 2012-12-19 | 京东方科技集团股份有限公司 | Resin composition of negative photoresist and preparation method thereof |
| CN103995436A (en) * | 2013-02-15 | 2014-08-20 | 三星显示有限公司 | Photosensitive resin composition |
Non-Patent Citations (4)
| Title |
|---|
| 句红兵 等: "利用热分析对导电胶进行组分分析的研究", 《化学与黏合》 * |
| 周宇艳 等: "热重分析-傅里叶变换红外光谱分析无机物填充高分子复合材料的组分", 《理化检验 化学分册》 * |
| 李虎: "光刻胶用成膜树脂的合成及性能研究", 《中国博士学位论文全文数据库 工程科技I辑》 * |
| 白正伟: "测定混合物组成及组分含量的热重分析法", 《分析测试学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112557640A (en) * | 2020-12-28 | 2021-03-26 | 中蓝晨光化工有限公司 | Method for testing degree of substitution of condensed type silicone resin |
| CN113030148A (en) * | 2021-03-24 | 2021-06-25 | 浙江省林业科学研究院 | Microscopic on-line detection method for phase state change of water-soluble low-molecular-weight resin |
| CN113030148B (en) * | 2021-03-24 | 2023-02-03 | 浙江省林业科学研究院 | Microcosmic online detection method for phase state change of water-soluble low-molecular-weight resin |
| CN113804867A (en) * | 2021-09-27 | 2021-12-17 | 上海彤程电子材料有限公司 | Method for testing photoresist resin component |
| CN113804867B (en) * | 2021-09-27 | 2023-10-31 | 上海彤程电子材料有限公司 | Method for testing photoresist resin component |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110927207B (en) | 2022-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110927207B (en) | Method for testing photoresist resin component | |
| KR101371878B1 (en) | Photo- and/or thermo-curable copolymer, curable resin compositions, and cured articles | |
| CN102311371B (en) | Compound, polymer comprising the same and chemically amplified resist composition comprising the polymer | |
| KR20090046883A (en) | Curable resin composition and method for forming cured coating film | |
| Naylor Jr et al. | Nuclear magnetic resonance spectra of some fluorine‐containing polymers | |
| CN105542061B (en) | Middle high solid Hydroxylated acrylic resin and preparation method thereof | |
| KR20120049640A (en) | Composition for forming a photoresist top coat layer in extreme ultraviolet lithography and patterning method using the same | |
| TW200830050A (en) | Resist composition and pattern-forming method using the same | |
| CN113214468A (en) | Polyvinyl chloride plasticizing antistatic agent and preparation method thereof | |
| CN112694555A (en) | Deep ultraviolet positive photoresist film-forming resin and preparation method thereof | |
| JP5075691B2 (en) | Light and / or thermosetting copolymer, curable resin composition, and cured product | |
| CN109942741A (en) | A kind of preparation method of photoresist resin | |
| KR101312147B1 (en) | Synthesis of Photoresist Polymer | |
| KR100190012B1 (en) | Method of manufacturing base resin for chemically amplified resist | |
| TWI757816B (en) | Phosphorus-containing compound, manufacturing method thereof, flame-retardant unsaturated resin composition and thermoset | |
| TW201930458A (en) | Composition, insulating material employing the same, and method for preparing an insulating material | |
| Zhang et al. | Design of new benzoxazines with excellent thermal stability and processability using the “gold panning” method | |
| CN107778743A (en) | A kind of high intensity modified poly (methyl methacrylate) plastics | |
| CN112961323A (en) | Fluorinated benzonitrile and fluorinated epoxy resin composite material and preparation method thereof | |
| CN111704704A (en) | Ultrahigh-resolution anti-etching metal-containing block copolymer, and preparation and application thereof | |
| JP4691461B2 (en) | Positive resist composition and pattern forming method using the same | |
| KR102553747B1 (en) | UV-curable dismantling Pressure sensitive adhesive(PSA) composition and Manufacturing method thereof | |
| CN111116926B (en) | Preparation method of high-strength self-repairing material based on siloxane bond | |
| KR20100073562A (en) | Method for analyzing a composition of photosensitive resin copolymer using ft-nir | |
| JP2010202698A (en) | Production method of copolymer for semiconductor lithography |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20200721 Address after: Room 1005-1006, 1289 Baoshan Road, Dadan Street, Beilun District, Ningbo City, Zhejiang Province Applicant after: NINGBO NANDA OPTOELECTRONIC MATERIAL Co.,Ltd. Applicant after: JIANGSU NATA OPTO-ELECTRONIC MATERIAL Co.,Ltd. Address before: Room 1005-1006, 1289 Baoshan Road, Dadan Street, Beilun District, Ningbo City, Zhejiang Province Applicant before: NINGBO NANDA OPTOELECTRONIC MATERIAL Co.,Ltd. |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant |